The first game in the history of the Century League took place on April 22, 1876 with Boston visiting Philadelphia. The visiting squad won the game by a score of 5-2 with Boston's Ted Maston getting the first hit in league history and Daniel Fallow notching the victory. In honor of the Centennial Exhibition that would take place in Philadelphia that summer, the Philadelphia squad became known as the Centennials while Boston was dubbed the Pilgrims. 

The other clubs to take the field in that inaugural season included the Brooklyn Unions, St. Louis Brewers, Chicago Chiefs, Cincinnati Monarchs, New York Knights and Detroit Woodwards. Though William Whitney had used his extensive resources to acquire a very talented group for his Chicago club, it was the Brooklynites who won the first championship flag in Century League history. Miles Bigsby's club posted a stellar 52-14 record, four games better than Philadelphia's 45-15 mark. Cincinnati was third with a 40-29 mark. Brooklyn won largely due to the stellar work of its pitchers Leo Miller and Hartigan O'Carroll although they also had a potent lineup led by Cal Jones who recorded a .384 average to lead his club.

The rest of the league standings table shook out as follows: Boston in 4th with a 36-34 mark, Chicago (30-35), Detroit (26-43), New York (16-41), and St. Louis (15-49). 

Particularly surprising was the poor play of the New York club. With a roster full of familiar faces from their barnstorming days, the New Yorkers were expected to contend with Chicago for league honors. Instead they were terrible - and packed it in early, refusing to travel for their final road trip (Philadelphia did the same when they realized they couldn't catch Brooklyn). To add insult to injury, New York owner Charles Bigsby had to endure the taunts of his younger sibling who owned the Brooklyn club. Two of the clubs impacted by the early ending of the easterners' seasons were Cincinnati and St. Louis - and their ownership was irate.

Other individual performances of note included two Philadelphia players topping the .400 mark in 2B Roy Frazer (.430) and CF Jeffrey Nicks (.409). Chicago's Jack Wakeham hit .378 and Sabremetricians of the future would note that he had the best WAR in the league's inaugural season (4.6). On the pitching side, Cincinnati's Andrew Overton posted a 1.75 ERA and Boston's Daniel Fallow led the league in victories with 33 (Philly's Paul Kennett was just behind him with 32).

The first season had proved that the concept of a professional baseball league could work, but it wasn't all good news. The league was not yet a full calendar year old and William Whitney had his first crisis. When he refused to acquiesce to the demands of St. Louis and Cincinnati to expel the New York and Philadelphia clubs, Whitney saw the Monarchs and Brewers leave after just one season.